[2][3] He and fellow at-large incumbent Nancy K. Parker won re-election over nine challengers despite public displeasure regarding Labor Day weekend riots the previous year.

[15][16] In 1997, when Virginia Beach struck a deal with the PGA Tour to build a $10 million championship golf course, Sessoms was one of the city's spokespersons.

[21] Sessoms was sworn in on January 5, 2009, with the agenda to create jobs, improve the environment and neighborhoods, purchase Norfolk Southern Railway right-of-way to build a light-rail line, and address problems with youth gangs.

[27][28] On November 9, 2014, The Virginian-Pilot reported that Sessoms had "voted dozens of times with the City Council on matters directly benefiting developers who borrowed at least $140 million from the bank.

"[29] John Holland, writing for the newspaper, said "a review of some 3,000 court, land and council records showed a pattern of such votes spanning his nearly six years in office."

"[30] On November 11, 2014, on returning from an international trip, Sessoms issued a statement saying "I have been made aware of the recent stories and am taking this situation and these allegations seriously.

On the following day, the City of Virginia Beach Commonwealth's Attorney asked for a special prosecutor investigation if Sessoms broke laws by casting council votes in favor of bank clients.

[34] On December 24, 2014, Sessoms resigned from TowneBank, in accordance with a new policy prohibiting senior bank management from holding elective office.

[35] On November 4, 2015, Sessoms was charged with five misdemeanor counts of violating the state's Conflict of Interest Act for votes he cast that benefited borrowers of TowneBank.

[7] Until September 1988, he was a member of the board of directors of the Princess Anne Country Club, which was at the time an integration target by the National Association for the Advancement of Colored People.